ChemWiki - User contributions [en]

It:wilkinson

2006-12-06T19:45:28Z

Hcy05: /* Structure and Synthesis */

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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1.1431 1.9689 -3.0329 C 0 0 0 0 0
0.5202 1.6759 -4.2514 C 0 0 0 0 0
0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
3.8158 -4.8684 -1.5308 C 0 0 0 0 0
3.6375 -3.8077 -0.6402 C 0 0 0 0 0
1.6930 -2.8219 1.9100 C 0 0 0 0 0
2.4316 -2.9296 3.0942 C 0 0 0 0 0
2.0614 -3.8291 4.0967 C 0 0 0 0 0
0.9548 -4.6600 3.9209 C 0 0 0 0 0
0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
4.7485 0.6342 2.7897 C 0 0 0 0 0
3.6218 -0.0078 2.2721 C 0 0 0 0 0
2.1677 -1.6384 0.5153 P 0 3 0 0 0
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0
-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0
-0.7810 3.0491 -0.3062 C 0 0 0 0 0
-0.1187 3.2408 0.9128 C 0 0 0 0 0
0.2956 4.5106 1.3177 C 0 0 0 0 0
0.0355 5.6176 0.5096 C 0 0 0 0 0
-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
-0.4429 2.4148 -6.0491 H 0 0 0 0 0
-0.1140 4.8185 -5.4421 H 0 0 0 0 0
1.0451 5.3954 -3.3036 H 0 0 0 0 0
1.8069 3.6360 -1.7841 H 0 0 0 0 0
4.3314 1.8231 -3.0516 H 0 0 0 0 0
6.1490 3.2015 -2.0911 H 0 0 0 0 0
6.0335 3.9578 0.2887 H 0 0 0 0 0
4.0574 3.3374 1.6885 H 0 0 0 0 0
2.2746 1.8922 0.7534 H 0 0 0 0 0
0.6584 -1.3179 -3.8324 H 0 0 0 0 0
1.6220 -2.9883 -5.3441 H 0 0 0 0 0
4.0844 -3.4247 -5.3442 H 0 0 0 0 0
5.5606 -2.1234 -3.7998 H 0 0 0 0 0
4.6167 -0.4073 -2.3293 H 0 0 0 0 0
0.5148 -2.8211 -1.5913 H 0 0 0 0 0
0.8200 -4.7186 -3.1578 H 0 0 0 0 0
2.9459 -6.0336 -3.1421 H 0 0 0 0 0
4.7305 -5.4811 -1.4819 H 0 0 0 0 0
4.4065 -3.6300 0.1274 H 0 0 0 0 0
3.3326 -2.3235 3.2645 H 0 0 0 0 0
2.6540 -3.8952 5.0239 H 0 0 0 0 0
0.6662 -5.3756 4.7074 H 0 0 0 0 0
-0.6272 -5.2652 2.5700 H 0 0 0 0 0
0.0300 -3.6842 0.7953 H 0 0 0 0 0
5.0569 -1.5000 -0.4374 H 0 0 0 0 0
7.0365 -0.3324 0.4516 H 0 0 0 0 0
6.8657 1.0364 2.5360 H 0 0 0 0 0
4.6632 1.2478 3.7011 H 0 0 0 0 0
2.6569 0.1188 2.7908 H 0 0 0 0 0
-3.1849 2.7955 -2.5425 H 0 0 0 0 0
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-3.4716 0.1205 -5.9078 H 0 0 0 0 0
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0
0.0849 2.3852 1.5776 H 0 0 0 0 0
0.8246 4.6387 2.2757 H 0 0 0 0 0
0.3629 6.6219 0.8221 H 0 0 0 0 0
-0.8555 6.3149 -1.3365 H 0 0 0 0 0
-1.5785 4.0746 -2.0551 H 0 0 0 0 0
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0
-5.2797 -1.3605 0.6443 H 0 0 0 0 0
-6.1750 0.3688 2.2115 H 0 0 0 0 0
-4.9429 2.5200 2.5189 H 0 0 0 0 0
-2.8474 2.9476 1.2892 H 0 0 0 0 0
1 20 1 6 0 0
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1 41 1 0 0 0
2 3 2 0 0 0
2 7 1 0 0 0
2 20 1 1 0 0
3 4 1 6 0 0
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5 6 1 1 0 0
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6 7 2 0 0 0
6 63 1 0 0 0
7 64 1 1 0 0
8 9 2 0 0 0
8 13 1 1 0 0
8 20 1 0 0 0
9 10 1 0 0 0
9 65 1 6 0 0
10 11 2 0 0 0
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11 12 1 1 0 0
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12 13 2 0 0 0
12 68 1 1 0 0
13 69 1 1 0 0
14 15 2 0 0 0
14 19 1 0 0 0
14 20 1 1 0 0
15 16 1 6 0 0
15 70 1 0 0 0
16 17 2 0 0 0
16 71 1 6 0 0
17 18 1 1 0 0
17 72 1 6 0 0
18 19 2 0 0 0
18 73 1 0 0 0
19 74 1 1 0 0
21 22 2 0 0 0
21 26 1 0 0 0
21 39 1 1 0 0
22 23 1 6 0 0
22 75 1 0 0 0
23 24 2 0 0 0
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24 25 1 1 0 0
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25 26 2 0 0 0
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26 79 1 1 0 0
27 28 2 0 0 0
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28 29 1 1 0 0
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29 30 2 0 0 0
29 81 1 1 0 0
30 31 1 6 0 0
30 82 1 1 0 0
31 32 2 0 0 0
31 83 1 0 0 0
32 84 1 6 0 0
33 34 2 0 0 0
33 38 1 1 0 0
33 39 1 0 0 0
34 35 1 0 0 0
34 85 1 6 0 0
35 36 2 0 0 0
35 86 1 6 0 0
36 37 1 1 0 0
36 87 1 0 0 0
37 38 2 0 0 0
37 88 1 1 0 0
38 89 1 1 0 0
41 42 1 6 0 0
41 48 1 0 0 0
41 54 1 1 0 0
42 43 2 0 0 0
42 47 1 0 0 0
43 44 1 6 0 0
43 90 1 1 0 0
44 45 2 0 0 0
44 91 1 0 0 0
45 46 1 1 0 0
45 92 1 6 0 0
46 47 2 0 0 0
46 93 1 0 0 0
47 94 1 1 0 0
48 49 2 0 0 0
48 53 1 6 0 0
49 50 1 0 0 0
49 95 1 1 0 0
50 51 2 0 0 0
50 96 1 1 0 0
51 52 1 6 0 0
51 97 1 0 0 0
52 53 2 0 0 0
52 98 1 6 0 0
53 99 1 6 0 0
54 55 2 0 0 0
54 59 1 1 0 0
55 56 1 1 0 0
55100 1 6 0 0
56 57 2 0 0 0
56101 1 0 0 0
57 58 1 0 0 0
57102 1 1 0 0
58 59 2 0 0 0
58103 1 1 0 0
59104 1 0 0 0
M END</inlineContents>
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The formula for Wilkinsons Catalyst is C54H45ClP3Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==
Wilkinson catalyst is a square planar complex which has a molecular formula of RhCl(PPh3)3. It can be prepared by mixing rhodium trichloride and triphenylphosphine in ethanol and refluxing for 2-3 hrs.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

[[image:Wilkinson_Catalyst1.JPG]]

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

Wilkinson catalyst is widely used in a hydrogenation of alkene. Let’s consider in the hydrogenation of propylene (C3H6). At first, the chlorotrisr(triphenylphosphine)rhodium(I) lose a triphenylphosphine group and become a trigonal planar complex. Note the oxidation state of rhodium is still (I). Then Addition of H2 to the central metal atom results in a trigonal bipyramid complex. Now the oxidation state of rhodium has changed to (III). Then propylene will attack the central atom and a transition state which the central atom has 6 coordinates (octahedral complex). The propylene is then very quickly comes off with the 2 hydrogen and reduce to an alkane (propane). The catalyst is back to a trigonal planar complex at this stage and can be used to catalyst the hydrogenation of the next propylene molecule.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [|http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
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The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al2O3 surface to catalyse the hydrogenation reaction of olefins.

Ref:

[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d Journal of Molecular Catalysis A: Chemical Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152]

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C54H45ClP3Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:wilkinson

2006-12-06T19:44:31Z

Hcy05: /* Structure and Synthesis */

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
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3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
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-3.0491 0.3654 -4.9203 C 0 0 0 0 0
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-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
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The formula for Wilkinsons Catalyst is C54H45ClP3Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==
Wilkinson catalyst is a square planar complex which has a molecular formula of RhCl(PPh3)3. It can be prepared by mixing rhodium trichloride and triphenylphosphine in ethanol and refluxing for 2-3 hrs.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

[[image:Wilkinson_Catalyst1.JPG]]

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

Wilkinson catalyst is widely used in a hydrogenation of alkene. Let’s consider in the hydrogenation of propylene (C3H6). At first, the chlorotrisr(triphenylphosphine)rhodium(I) lose a triphenylphosphine group and become a trigonal planar complex. Note the oxidation state of rhodium is still (I). Then Addition of H2 to the central metal atom results in a trigonal bipyramid complex. Now the oxidation state of rhodium has changed to (III). Then propylene will attack the central atom and a transition state which the central atom has 6 coordinates (octahedral complex). The propylene is then very quickly comes off with the 2 hydrogen and reduce to an alkane (propane). The catalyst is back to a trigonal planar complex at this stage and can be used to catalyst the hydrogenation of the next propylene molecule.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
END</inlineContents>
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The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al2O3 surface to catalyse the hydrogenation reaction of olefins.

Ref:

[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d Journal of Molecular Catalysis A: Chemical Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152]

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C54H45ClP3Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:wilkinson

2006-12-06T19:44:15Z

Hcy05: /* Structure and Synthesis */

It:wilkinson

2006-12-06T19:43:40Z

Hcy05: /* Structure and Synthesis */

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
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3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
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2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
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0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
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3.6218 -0.0078 2.2721 C 0 0 0 0 0
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-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0
-0.7810 3.0491 -0.3062 C 0 0 0 0 0
-0.1187 3.2408 0.9128 C 0 0 0 0 0
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0.0355 5.6176 0.5096 C 0 0 0 0 0
-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
-0.4429 2.4148 -6.0491 H 0 0 0 0 0
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2.2746 1.8922 0.7534 H 0 0 0 0 0
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The formula for Wilkinsons Catalyst is C54H45ClP3Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==
Wilkinson catalyst is a square planar complex which has a molecular formula of RhCl(PPh3)3. It can be prepared by mixing rhodium trichloride and triphenylphosphine in ethanol and refluxing for 2-3 hrs.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

[[image:Wilkinson_Catalyst1.JPG]]

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

Wilkinson catalyst is widely used in a hydrogenation of alkene. Let’s consider in the hydrogenation of propylene (C3H6). At first, the chlorotrisr(triphenylphosphine)rhodium(I) lose a triphenylphosphine group and become a trigonal planar complex. Note the oxidation state of rhodium is still (I). Then Addition of H2 to the central metal atom results in a trigonal bipyramid complex. Now the oxidation state of rhodium has changed to (III). Then propylene will attack the central atom and a transition state which the central atom has 6 coordinates (octahedral complex). The propylene is then very quickly comes off with the 2 hydrogen and reduce to an alkane (propane). The catalyst is back to a trigonal planar complex at this stage and can be used to catalyst the hydrogenation of the next propylene molecule.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [[http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]|http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
END</inlineContents>
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The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al2O3 surface to catalyse the hydrogenation reaction of olefins.

Ref:

[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d Journal of Molecular Catalysis A: Chemical Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152]

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C54H45ClP3Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:wilkinson

2006-12-06T19:42:58Z

Hcy05: /* Structure and Synthesis */

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
3.8158 -4.8684 -1.5308 C 0 0 0 0 0
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1.6930 -2.8219 1.9100 C 0 0 0 0 0
2.4316 -2.9296 3.0942 C 0 0 0 0 0
2.0614 -3.8291 4.0967 C 0 0 0 0 0
0.9548 -4.6600 3.9209 C 0 0 0 0 0
0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
4.7485 0.6342 2.7897 C 0 0 0 0 0
3.6218 -0.0078 2.2721 C 0 0 0 0 0
2.1677 -1.6384 0.5153 P 0 3 0 0 0
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0
-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0
-0.7810 3.0491 -0.3062 C 0 0 0 0 0
-0.1187 3.2408 0.9128 C 0 0 0 0 0
0.2956 4.5106 1.3177 C 0 0 0 0 0
0.0355 5.6176 0.5096 C 0 0 0 0 0
-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
-0.4429 2.4148 -6.0491 H 0 0 0 0 0
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1.0451 5.3954 -3.3036 H 0 0 0 0 0
1.8069 3.6360 -1.7841 H 0 0 0 0 0
4.3314 1.8231 -3.0516 H 0 0 0 0 0
6.1490 3.2015 -2.0911 H 0 0 0 0 0
6.0335 3.9578 0.2887 H 0 0 0 0 0
4.0574 3.3374 1.6885 H 0 0 0 0 0
2.2746 1.8922 0.7534 H 0 0 0 0 0
0.6584 -1.3179 -3.8324 H 0 0 0 0 0
1.6220 -2.9883 -5.3441 H 0 0 0 0 0
4.0844 -3.4247 -5.3442 H 0 0 0 0 0
5.5606 -2.1234 -3.7998 H 0 0 0 0 0
4.6167 -0.4073 -2.3293 H 0 0 0 0 0
0.5148 -2.8211 -1.5913 H 0 0 0 0 0
0.8200 -4.7186 -3.1578 H 0 0 0 0 0
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The formula for Wilkinsons Catalyst is C54H45ClP3Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==
Wilkinson catalyst is a square planar complex which has a molecular formula of RhCl(PPh3)3. It can be prepared by mixing rhodium trichloride and triphenylphosphine in ethanol and refluxing for 2-3 hrs.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

[[image:Wilkinson_Catalyst1.JPG]]

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

Wilkinson catalyst is widely used in a hydrogenation of alkene. Let’s consider in the hydrogenation of propylene (C3H6). At first, the chlorotrisr(triphenylphosphine)rhodium(I) lose a triphenylphosphine group and become a trigonal planar complex. Note the oxidation state of rhodium is still (I). Then Addition of H2 to the central metal atom results in a trigonal bipyramid complex. Now the oxidation state of rhodium has changed to (III). Then propylene will attack the central atom and a transition state which the central atom has 6 coordinates (octahedral complex). The propylene is then very quickly comes off with the 2 hydrogen and reduce to an alkane (propane). The catalyst is back to a trigonal planar complex at this stage and can be used to catalyst the hydrogenation of the next propylene molecule.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [[http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html|http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
END</inlineContents>
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The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al2O3 surface to catalyse the hydrogenation reaction of olefins.

Ref:

[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d Journal of Molecular Catalysis A: Chemical Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152]

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C54H45ClP3Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:wilkinson

2006-12-06T19:26:23Z

Hcy05:

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
3.8158 -4.8684 -1.5308 C 0 0 0 0 0
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2.4316 -2.9296 3.0942 C 0 0 0 0 0
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0.9548 -4.6600 3.9209 C 0 0 0 0 0
0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
4.7485 0.6342 2.7897 C 0 0 0 0 0
3.6218 -0.0078 2.2721 C 0 0 0 0 0
2.1677 -1.6384 0.5153 P 0 3 0 0 0
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0
-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0
-0.7810 3.0491 -0.3062 C 0 0 0 0 0
-0.1187 3.2408 0.9128 C 0 0 0 0 0
0.2956 4.5106 1.3177 C 0 0 0 0 0
0.0355 5.6176 0.5096 C 0 0 0 0 0
-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
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1.0451 5.3954 -3.3036 H 0 0 0 0 0
1.8069 3.6360 -1.7841 H 0 0 0 0 0
4.3314 1.8231 -3.0516 H 0 0 0 0 0
6.1490 3.2015 -2.0911 H 0 0 0 0 0
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4.0574 3.3374 1.6885 H 0 0 0 0 0
2.2746 1.8922 0.7534 H 0 0 0 0 0
0.6584 -1.3179 -3.8324 H 0 0 0 0 0
1.6220 -2.9883 -5.3441 H 0 0 0 0 0
4.0844 -3.4247 -5.3442 H 0 0 0 0 0
5.5606 -2.1234 -3.7998 H 0 0 0 0 0
4.6167 -0.4073 -2.3293 H 0 0 0 0 0
0.5148 -2.8211 -1.5913 H 0 0 0 0 0
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3.3326 -2.3235 3.2645 H 0 0 0 0 0
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The formula for Wilkinsons Catalyst is C54H45ClP3Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==
Wilkinson catalyst is a square planar complex which has a molecular formula of RhCl(PPh3)3. It can be prepared by mixing rhodium trichloride and triphenylphosphine in ethanol and refluxing for 2-3 hrs.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

[[image:Wilkinson_Catalyst1.JPG]]

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

In hydrogenation of an alken: Before activation, RhCl(PPh3)3 is a ''square planar'' complex in which rhodium is in oxidation state 1. Then it loses one of the phenylphosine group. Dihydrogen, H2, is then homolytically dissociates into two hydrogen atoms which each coordinate to the rhodium oxidative addition: the metal's oxidation number increases to 3. The resulting ''octahedral'' complex then loses one of its phosphine ligands, which is replaced by the alkene.

One of the hydrogen atoms then transfers from the rhodium to the alkene, which becomes an alkyl ligand. The expelled phosphine ligand resumes its place in the complex and the remaining hydrogen then also transfers to the alkyl ligand, which becomes an alkane and leaves the complex. Thus the original Wilkinson complex, with all three phosphine ligands, is restored.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [[http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
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The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al2O3 surface to catalyse the hydrogenation reaction of olefins.

Ref:

[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d Journal of Molecular Catalysis A: Chemical Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152]

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C54H45ClP3Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

It:wilkinson

2006-12-06T19:14:53Z

Hcy05:

==Wilkinson's Catalyst==

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

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1.1431 1.9689 -3.0329 C 0 0 0 0 0
0.5202 1.6759 -4.2514 C 0 0 0 0 0
0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
3.8158 -4.8684 -1.5308 C 0 0 0 0 0
3.6375 -3.8077 -0.6402 C 0 0 0 0 0
1.6930 -2.8219 1.9100 C 0 0 0 0 0
2.4316 -2.9296 3.0942 C 0 0 0 0 0
2.0614 -3.8291 4.0967 C 0 0 0 0 0
0.9548 -4.6600 3.9209 C 0 0 0 0 0
0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
4.7485 0.6342 2.7897 C 0 0 0 0 0
3.6218 -0.0078 2.2721 C 0 0 0 0 0
2.1677 -1.6384 0.5153 P 0 3 0 0 0
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0
-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0
-0.7810 3.0491 -0.3062 C 0 0 0 0 0
-0.1187 3.2408 0.9128 C 0 0 0 0 0
0.2956 4.5106 1.3177 C 0 0 0 0 0
0.0355 5.6176 0.5096 C 0 0 0 0 0
-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
-0.4429 2.4148 -6.0491 H 0 0 0 0 0
-0.1140 4.8185 -5.4421 H 0 0 0 0 0
1.0451 5.3954 -3.3036 H 0 0 0 0 0
1.8069 3.6360 -1.7841 H 0 0 0 0 0
4.3314 1.8231 -3.0516 H 0 0 0 0 0
6.1490 3.2015 -2.0911 H 0 0 0 0 0
6.0335 3.9578 0.2887 H 0 0 0 0 0
4.0574 3.3374 1.6885 H 0 0 0 0 0
2.2746 1.8922 0.7534 H 0 0 0 0 0
0.6584 -1.3179 -3.8324 H 0 0 0 0 0
1.6220 -2.9883 -5.3441 H 0 0 0 0 0
4.0844 -3.4247 -5.3442 H 0 0 0 0 0
5.5606 -2.1234 -3.7998 H 0 0 0 0 0
4.6167 -0.4073 -2.3293 H 0 0 0 0 0
0.5148 -2.8211 -1.5913 H 0 0 0 0 0
0.8200 -4.7186 -3.1578 H 0 0 0 0 0
2.9459 -6.0336 -3.1421 H 0 0 0 0 0
4.7305 -5.4811 -1.4819 H 0 0 0 0 0
4.4065 -3.6300 0.1274 H 0 0 0 0 0
3.3326 -2.3235 3.2645 H 0 0 0 0 0
2.6540 -3.8952 5.0239 H 0 0 0 0 0
0.6662 -5.3756 4.7074 H 0 0 0 0 0
-0.6272 -5.2652 2.5700 H 0 0 0 0 0
0.0300 -3.6842 0.7953 H 0 0 0 0 0
5.0569 -1.5000 -0.4374 H 0 0 0 0 0
7.0365 -0.3324 0.4516 H 0 0 0 0 0
6.8657 1.0364 2.5360 H 0 0 0 0 0
4.6632 1.2478 3.7011 H 0 0 0 0 0
2.6569 0.1188 2.7908 H 0 0 0 0 0
-3.1849 2.7955 -2.5425 H 0 0 0 0 0
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-3.4716 0.1205 -5.9078 H 0 0 0 0 0
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0
0.0849 2.3852 1.5776 H 0 0 0 0 0
0.8246 4.6387 2.2757 H 0 0 0 0 0
0.3629 6.6219 0.8221 H 0 0 0 0 0
-0.8555 6.3149 -1.3365 H 0 0 0 0 0
-1.5785 4.0746 -2.0551 H 0 0 0 0 0
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0
-5.2797 -1.3605 0.6443 H 0 0 0 0 0
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1 41 1 0 0 0
2 3 2 0 0 0
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10 11 2 0 0 0
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12 13 2 0 0 0
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13 69 1 1 0 0
14 15 2 0 0 0
14 19 1 0 0 0
14 20 1 1 0 0
15 16 1 6 0 0
15 70 1 0 0 0
16 17 2 0 0 0
16 71 1 6 0 0
17 18 1 1 0 0
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18 19 2 0 0 0
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21 22 2 0 0 0
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The formula for Wilkinsons Catalyst is C54H45ClP3Rh

==An example of the Wilkinson Catalyst reaction:==
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2]. When the pyridine reacts with the catalyst, a solution forms and chemists are then able to study the selectivity of the catalyst as to maximise its role as a catalyst.

2.J. Chem. Soc., Dalton Trans., 1994, 2875 - 2880, DOI: 10.1039/DT9940002875

==Structure and Synthesis==

This compound RhCl(PPh3) is a ''square planar'', 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of ''rhodium trichloride'' with ''triphenylphosphine''. The synthesis is conducted in refluxing ethanol.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

[[image:Wilkinson_Catalyst1.JPG]]

[[Image:Wilkinson_Catalyst.GIF|thumb|A scheme showing how the catalyst works]]

In hydrogenation of an alken: Before activation, RhCl(PPh3)3 is a ''square planar'' complex in which rhodium is in oxidation state 1. Then it loses one of the phenylphosine group. Dihydrogen, H2, is then homolytically dissociates into two hydrogen atoms which each coordinate to the rhodium oxidative addition: the metal's oxidation number increases to 3. The resulting ''octahedral'' complex then loses one of its phosphine ligands, which is replaced by the alkene.

One of the hydrogen atoms then transfers from the rhodium to the alkene, which becomes an alkyl ligand. The expelled phosphine ligand resumes its place in the complex and the remaining hydrogen then also transfers to the alkyl ligand, which becomes an alkane and leaves the complex. Thus the original Wilkinson complex, with all three phosphine ligands, is restored.

The link below contain an animation which show how the H2 and the alkene attach to the metal centre. [[http://www.ncl.ox.ac.uk/quicktime/hydrogenation.html]]

==A brief history of the Wilkinson catalyst:==
The catalyst is named after Profesor Sir Geoffrey Wilkinson who won a Nobel Laureate for chemistry. The structure as you can see above is organometallic and 'activates' small molecules therefore the catalyst lowers the activation energies for bond making and bond breaking. Profesor Wilkinson himself was involved heavily in the inorganic field and pioneered the organometallic chemistry age.

http://www.3dchem.com/molecules.asp?ID=35#

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<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY TPPRHC01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 19.470 12.689 18.202 90.00 90.00 90.00 P n a 21 4
ATOM 1 Rh1 UNK 0 1 1.227 0.367 4.551 1.00 0.00
ATOM 2 Cl1 UNK 0 1 -0.989 0.921 3.801 1.00 0.00
ATOM 3 P1 UNK 0 1 1.558 2.646 4.651 1.00 0.00
ATOM 4 P2 UNK 0 1 3.355 -0.253 4.745 1.00 0.00
ATOM 5 P3 UNK 0 1 0.300 -1.728 5.018 1.00 0.00
ATOM 6 C1 UNK 0 1 0.481 3.464 5.897 1.00 0.00
ATOM 7 C2 UNK 0 1 0.724 4.784 6.260 1.00 0.00
ATOM 8 C3 UNK 0 1 -0.105 5.416 7.181 1.00 0.00
ATOM 9 C4 UNK 0 1 -1.178 4.733 7.741 1.00 0.00
ATOM 10 C5 UNK 0 1 -1.421 3.401 7.379 1.00 0.00
ATOM 11 C6 UNK 0 1 -0.594 2.771 6.458 1.00 0.00
ATOM 12 C7 UNK 0 1 1.180 3.528 3.093 1.00 0.00
ATOM 13 C8 UNK 0 1 1.279 2.774 1.928 1.00 0.00
ATOM 14 C9 UNK 0 1 1.069 3.375 0.690 1.00 0.00
ATOM 15 C10 UNK 0 1 0.757 4.733 0.617 1.00 0.00
ATOM 16 C11 UNK 0 1 0.658 5.484 1.782 1.00 0.00
ATOM 17 C12 UNK 0 1 0.868 4.885 3.020 1.00 0.00
ATOM 18 C13 UNK 0 1 3.154 3.416 5.129 1.00 0.00
ATOM 19 C14 UNK 0 1 3.913 4.126 4.201 1.00 0.00
ATOM 20 C15 UNK 0 1 5.089 4.753 4.605 1.00 0.00
ATOM 21 C16 UNK 0 1 5.510 4.670 5.923 1.00 0.00
ATOM 22 C17 UNK 0 1 4.751 3.958 6.849 1.00 0.00
ATOM 23 C18 UNK 0 1 3.577 3.331 6.462 1.00 0.00
ATOM 24 C19 UNK 0 1 4.665 0.803 4.004 1.00 0.00
ATOM 25 C20 UNK 0 1 4.517 1.081 2.641 1.00 0.00
ATOM 26 C21 UNK 0 1 5.491 1.807 1.968 1.00 0.00
ATOM 27 C22 UNK 0 1 6.622 2.255 2.657 1.00 0.00
ATOM 28 C23 UNK 0 1 6.776 1.978 4.006 1.00 0.00
ATOM 29 C24 UNK 0 1 5.802 1.252 4.680 1.00 0.00
ATOM 30 C25 UNK 0 1 3.670 -1.769 3.726 1.00 0.00
ATOM 31 C26 UNK 0 1 2.884 -1.902 2.585 1.00 0.00
ATOM 32 C27 UNK 0 1 3.102 -2.957 1.709 1.00 0.00
ATOM 33 C28 UNK 0 1 4.106 -3.888 1.975 1.00 0.00
ATOM 34 C29 UNK 0 1 4.893 -3.755 3.116 1.00 0.00
ATOM 35 C30 UNK 0 1 4.675 -2.690 3.992 1.00 0.00
ATOM 36 C31 UNK 0 1 3.972 -0.558 6.480 1.00 0.00
ATOM 37 C32 UNK 0 1 5.218 -1.104 6.771 1.00 0.00
ATOM 38 C33 UNK 0 1 5.605 -1.320 8.100 1.00 0.00
ATOM 39 C34 UNK 0 1 4.751 -0.964 9.137 1.00 0.00
ATOM 40 C35 UNK 0 1 3.505 -0.406 8.846 1.00 0.00
ATOM 41 C36 UNK 0 1 3.117 -0.203 7.517 1.00 0.00
ATOM 42 C37 UNK 0 1 -1.038 -1.377 6.254 1.00 0.00
ATOM 43 C38 UNK 0 1 -0.738 -0.510 7.303 1.00 0.00
ATOM 44 C39 UNK 0 1 -1.706 -0.212 8.258 1.00 0.00
ATOM 45 C40 UNK 0 1 -2.973 -0.778 8.165 1.00 0.00
ATOM 46 C41 UNK 0 1 -3.275 -1.643 7.119 1.00 0.00
ATOM 47 C42 UNK 0 1 -2.307 -1.943 6.161 1.00 0.00
ATOM 48 C43 UNK 0 1 1.264 -3.073 5.839 1.00 0.00
ATOM 49 C44 UNK 0 1 1.879 -4.060 5.069 1.00 0.00
ATOM 50 C45 UNK 0 1 2.658 -5.035 5.681 1.00 0.00
ATOM 51 C46 UNK 0 1 2.821 -5.031 7.062 1.00 0.00
ATOM 52 C47 UNK 0 1 2.206 -4.048 7.834 1.00 0.00
ATOM 53 C48 UNK 0 1 1.427 -3.069 7.223 1.00 0.00
ATOM 54 C49 UNK 0 1 -0.541 -2.690 3.708 1.00 0.00
ATOM 55 C50 UNK 0 1 -0.641 -2.122 2.439 1.00 0.00
ATOM 56 C51 UNK 0 1 -1.266 -2.817 1.411 1.00 0.00
ATOM 57 C52 UNK 0 1 -1.793 -4.086 1.649 1.00 0.00
ATOM 58 C53 UNK 0 1 -1.694 -4.656 2.918 1.00 0.00
ATOM 59 C54 UNK 0 1 -1.069 -3.959 3.946 1.00 0.00
ATOM 60 H1 UNK 0 1 1.499 5.279 5.861 1.00 0.00
ATOM 61 H2 UNK 0 1 0.078 6.357 7.463 1.00 0.00
ATOM 62 H3 UNK 0 1 -1.772 5.177 8.409 1.00 0.00
ATOM 63 H4 UNK 0 1 -2.181 2.906 7.772 1.00 0.00
ATOM 64 H5 UNK 0 1 -0.759 1.827 6.189 1.00 0.00
ATOM 65 H6 UNK 0 1 1.499 1.802 1.984 1.00 0.00
ATOM 66 H7 UNK 0 1 1.149 2.830 -0.146 1.00 0.00
ATOM 67 H8 UNK 0 1 0.604 5.164 -0.273 1.00 0.00
ATOM 68 H9 UNK 0 1 0.428 6.459 1.729 1.00 0.00
ATOM 69 H10 UNK 0 1 0.798 5.418 3.859 1.00 0.00
ATOM 70 H11 UNK 0 1 3.621 4.200 3.258 1.00 0.00
ATOM 71 H12 UNK 0 1 5.646 5.279 3.968 1.00 0.00
ATOM 72 H13 UNK 0 1 6.347 5.114 6.243 1.00 0.00
ATOM 73 H14 UNK 0 1 5.043 3.870 7.809 1.00 0.00
ATOM 74 H15 UNK 0 1 3.018 2.804 7.117 1.00 0.00
ATOM 75 H16 UNK 0 1 3.699 0.761 2.148 1.00 0.00
ATOM 76 H17 UNK 0 1 5.393 2.005 0.983 1.00 0.00
ATOM 77 H18 UNK 0 1 7.321 2.779 2.166 1.00 0.00
ATOM 78 H19 UNK 0 1 7.593 2.297 4.496 1.00 0.00
ATOM 79 H20 UNK 0 1 5.899 1.053 5.643 1.00 0.00
ATOM 80 H21 UNK 0 1 2.161 -1.231 2.403 1.00 0.00
ATOM 81 H22 UNK 0 1 2.531 -3.058 0.892 1.00 0.00
ATOM 82 H23 UNK 0 1 4.264 -4.644 1.347 1.00 0.00
ATOM 83 H24 UNK 0 1 5.607 -4.428 3.295 1.00 0.00
ATOM 84 H25 UNK 0 1 5.237 -2.601 4.805 1.00 0.00
ATOM 85 H26 UNK 0 1 5.841 -1.358 6.025 1.00 0.00
ATOM 86 H27 UNK 0 1 6.503 -1.713 8.318 1.00 0.00
ATOM 87 H28 UNK 0 1 5.004 -1.104 10.084 1.00 0.00
ATOM 88 H29 UNK 0 1 2.882 -0.152 9.592 1.00 0.00
ATOM 89 H30 UNK 0 1 2.220 0.190 7.317 1.00 0.00
ATOM 90 H31 UNK 0 1 0.175 -0.102 7.372 1.00 0.00
ATOM 91 H32 UNK 0 1 -1.499 0.406 9.010 1.00 0.00
ATOM 92 H33 UNK 0 1 -3.660 -0.571 8.846 1.00 0.00
ATOM 93 H34 UNK 0 1 -4.186 -2.056 7.044 1.00 0.00
ATOM 94 H35 UNK 0 1 -2.531 -2.563 5.406 1.00 0.00
ATOM 95 H36 UNK 0 1 1.772 -4.073 4.077 1.00 0.00
ATOM 96 H37 UNK 0 1 3.115 -5.748 5.151 1.00 0.00
ATOM 97 H38 UNK 0 1 3.368 -5.723 7.536 1.00 0.00
ATOM 98 H39 UNK 0 1 2.317 -4.035 8.846 1.00 0.00
ATOM 99 H40 UNK 0 1 0.974 -2.360 7.772 1.00 0.00
ATOM 100 H41 UNK 0 1 -0.253 -1.218 2.257 1.00 0.00
ATOM 101 H42 UNK 0 1 -1.343 -2.424 0.491 1.00 0.00
ATOM 102 H43 UNK 0 1 -2.239 -4.606 0.910 1.00 0.00
ATOM 103 H44 UNK 0 1 -2.083 -5.570 3.094 1.00 0.00
ATOM 104 H45 UNK 0 1 -0.993 -4.352 4.860 1.00 0.00
CONECT 1 2 3 4 5
CONECT 2 1
CONECT 3 1 6 12 18
CONECT 4 1 24 30 36
CONECT 5 1 42 48 54
CONECT 6 3 7 11
CONECT 7 6 8 60
CONECT 8 7 9 61
CONECT 9 8 10 62
CONECT 10 9 11 63
CONECT 11 6 10 64
CONECT 12 3 13 17
CONECT 13 12 14 65
CONECT 14 13 15 66
CONECT 15 14 16 67
CONECT 16 15 17 68
CONECT 17 12 16 69
CONECT 18 3 19 23
CONECT 19 18 20 70
CONECT 20 19 21 71
CONECT 21 20 22 72
CONECT 22 21 23 73
CONECT 23 18 22 74
CONECT 24 4 25 29
CONECT 25 24 26 75
CONECT 26 25 27 76
CONECT 27 26 28 77
CONECT 28 27 29 78
CONECT 29 24 28 79
CONECT 30 4 31 35
CONECT 31 30 32 80
CONECT 32 31 33 81
CONECT 33 32 34 82
CONECT 34 33 35 83
CONECT 35 30 34 84
CONECT 36 4 37 41
CONECT 37 36 38 85
CONECT 38 37 39 86
CONECT 39 38 40 87
CONECT 40 39 41 88
CONECT 41 36 40 89
CONECT 42 5 43 47
CONECT 43 42 44 90
CONECT 44 43 45 91
CONECT 45 44 46 92
CONECT 46 45 47 93
CONECT 47 42 46 94
CONECT 48 5 49 53
CONECT 49 48 50 95
CONECT 50 49 51 96
CONECT 51 50 52 97
CONECT 52 51 53 98
CONECT 53 48 52 99
CONECT 54 5 55 59
CONECT 55 54 56 100
CONECT 56 55 57 101
CONECT 57 56 58 102
CONECT 58 57 59 103
CONECT 59 54 58 104
CONECT 60 7
CONECT 61 8
CONECT 62 9
CONECT 63 10
CONECT 64 11
CONECT 65 13
CONECT 66 14
CONECT 67 15
CONECT 68 16
CONECT 69 17
CONECT 70 19
CONECT 71 20
CONECT 72 21
CONECT 73 22
CONECT 74 23
CONECT 75 25
CONECT 76 26
CONECT 77 27
CONECT 78 28
CONECT 79 29
CONECT 80 31
CONECT 81 32
CONECT 82 33
CONECT 83 34
CONECT 84 35
CONECT 85 37
CONECT 86 38
CONECT 87 39
CONECT 88 40
CONECT 89 41
CONECT 90 43
CONECT 91 44
CONECT 92 45
CONECT 93 46
CONECT 94 47
CONECT 95 49
CONECT 96 50
CONECT 97 51
CONECT 98 52
CONECT 99 53
CONECT 100 55
CONECT 101 56
CONECT 102 57
CONECT 103 58
CONECT 104 59
MASTER 0 0 0 0 0 0 0 0 104 0 104 0
END</inlineContents>
</jmolApplet>
</jmol>

The above 3D picture was firstly drawn in the ConQuest programme using 2D tools and then a search for the 3D molecule was made giving the following hit as you see.

==Comparison with other catalysts:==
Two other famous catalysts used in many chemical reactions are Ni and Pd and these comoplexes can be better or worse than the Wilkinson catalyst in some properties. For example, the Wilkinson catalyst is more active and so faster reactions are possible. This is shown by comparing therate constants in the table below as the magnitude of k is largest for the Wilkinson catalyst. Another advantage of this catalyst is that in comparison with the reactant and product phases, the catalyst can either be homogeneous or heterogeneous, whilst the other 2 catalyst are normally in the solid phase.

[[Image:cattable.gif|thumb|centre|200|Comparison of the Wilkinson catalyst with Pd and Ni]]

With THT present (above in the table), the Rh complex will change its coordination by a larger amount but the Pd and Ni catalyst retain its original coordination number. Once again, this is better as a catalyst as the larger surface in the larger coordination sphere is able to act as an bigger active site for the reactants to attach to. Finally, the Rh catalyst shows a great resistance to sulphur poisoning with organic compounds containing S atoms but Pd and Ni do not. The Wilkinson catalyst works well when it is complexed to a γ-Al2O3 surface to catalyse the hydrogenation reaction of olefins.

Ref:

[http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TGM-3Y9RF5P-J&_coverDate=12%2F15%2F1999&_alid=475460761&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5258&_sort=d&view=c&_acct=C000011279&_version=1&_urlVersion=0&_userid=217827&md5=16c34de59089a2a3e11dc01745af7d7d Journal of Molecular Catalysis A: Chemical Volume 149, Issues 1-2 , 15 December 1999, Pages 147-152]

The Wilkinson catalyst is a well known homogeneous catalyst. The advantages of it being homogeneous rather than heterogeneous is that the catalyst is dissolved in with the reagents and therefore the rate of reaction is likely to be greater. Also the ligands on the catalyst can be 'tuned' as to achieve 'selective reductions'1. However, the separation of the catalyst from the reagents and products will be difficult as they are in the same phase.

1 = from the Organic Synthesis notes of Alan Armstrong.

==Olefin hydrogenation with the Wilkinson catalyst==
Adding to the above reaction scheme done by a collegeaue, the catalyst will react the olefin in the following ways to give transition stages on the way to the product.

[[Image:Stereochemwilk.GIF|thumb|centre|200|Description of image]]

The diagram shows the bond angles and bond lengths in angstroms. The angle of attack from the differing molecules is also shown according to experimental data.

Ref: J. Am. Chem. SOC. 1987, 109, 3455-3456

==References and External Links==

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

==Properties==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Wilkinson's catalyst'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Wilkinson's_catalyst1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''Chlorotris(triphenylphosphine)- rhodium''
|-
| [[CAS nummber]]
| 14694-95-2
|-
| [[Chemical formula]]
| {{{formula|C54H45ClP3Rh
|-
| [[Molecular mass]]
| {{{mol_mass|925.22 g/mol
|-
| [[Solubility in water]]
| {{{Solubility in water|Insoluble
|-
| [[Melting point]]
| {{{Melting point|245-250 °C
|-
| [[Appearance]]
| {{{Appearance| red solid
|-
| [[Coordination geometry]]
| {{{Coordination geometry| square planar
|}

File:Wilkinson Catalyst1.JPG

2006-12-06T19:14:03Z

Hcy05:

It:Oseltamivir

2006-12-06T18:56:17Z

Hcy05:

'''''Oseltamivir''''' is specially invented for treatment of influenzavirus A and B. It is neuraminidase inhibitors which stop the virus emerge from the infected cell. It is the first neuraminidase inhibitor which is orally active. It was first developed by Gilead sciences and is now available on the market with the trade name – tamiflu. However, in order to get this drug, prescription is needed.

'''Usage'''

When Tamiflu was first invented, it was used in treatment or prevention of influenza. Flu virus cause several symptoms to human body.
- Stuff nose
- Cough
- Sore throat
- Fever or chills
- Aches
- Tiredness
The use of tamiflu can reduce the recovery times and help the body to relief the symptoms. If the person is not infected by flu virus, he can still take tamiflu to prevent or minimise the chances of infection of influenza.

'''Dosage'''

The normal dosage of tamiflu if a person is infected by influenza is to take 2 tablets for in 5 days. For the prevention of flu (especially for those who is going to expose to the flu) is to take one tablet for at least a week.

'''How does it works'''

As mentioned above, Oseltamivir is a neuraminidase inhibitor. It binds to the surface of neuraminidase and stops its normal function. Neuraminidase is an enzyme which controls the release of the newly formed virus from the cell. So Oseltamivir does not actually kills the virus or stop its activity, it only stops the virus getting out from the cell. Therefore, when a patient is infected by flu virus, the virus can still replicate even a patient take tamiflu. However, the number of virus will not be huge enough to cause any flu symptoms to the patient if tamiflu is taken at the early stage. This has a very important consequence to the human body. With the help of tamiflu, the flu virus will be acuminated in a small area so the human immune systems can deal with the virus more efficiently.

'''Avian influenza'''

In 2005, tamiflu was first used in H5N1 influenza. However, normal dosage results in viral resistance. Therefore, patients required a higher doses and longer period of the drugs and it works quite well.

'''Structure of Oseltamivir'''

[[Image:Oseltamivir.bmp]]

==3D Structure==
<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 O1 MOL A 1 16.915 13.894 0.164 1.00 0.00
ATOM 2 C2 MOL A 1 15.808 12.929 -0.075 1.00 0.00
ATOM 3 C3 MOL A 1 16.850 15.311 -0.367 1.00 0.00
ATOM 4 C4 MOL A 1 14.629 13.131 0.985 1.00 0.00
ATOM 5 C5 MOL A 1 16.487 11.497 0.072 1.00 0.00
ATOM 6 C6 MOL A 1 15.676 16.256 0.137 1.00 0.00
ATOM 7 C7 MOL A 1 18.214 15.943 -0.120 1.00 0.00
ATOM 8 C8 MOL A 1 13.307 12.366 0.684 1.00 0.00
ATOM 9 C9 MOL A 1 15.611 10.259 -0.267 1.00 0.00
ATOM 10 N10 MOL A 1 14.381 15.721 -0.352 1.00 0.00
ATOM 11 C11 MOL A 1 15.933 17.639 -0.478 1.00 0.00
ATOM 12 C12 MOL A 1 18.374 17.256 0.063 1.00 0.00
ATOM 13 C13 MOL A 1 13.112 16.285 0.036 1.00 0.00
ATOM 14 N14 MOL A 1 14.886 18.618 -0.170 1.00 0.00
ATOM 15 C15 MOL A 1 17.219 18.192 0.124 1.00 0.00
ATOM 16 C16 MOL A 1 19.696 17.841 0.224 1.00 0.00
ATOM 17 C17 MOL A 1 11.842 15.745 -0.555 1.00 0.00
ATOM 18 O18 MOL A 1 13.058 17.198 0.865 1.00 0.00
ATOM 19 O19 MOL A 1 20.846 17.077 0.102 1.00 0.00
ATOM 20 O20 MOL A 1 19.789 19.052 0.436 1.00 0.00
ATOM 21 C21 MOL A 1 21.980 17.947 0.258 1.00 0.00
ATOM 22 C22 MOL A 1 23.282 17.163 0.030 1.00 0.00
ATOM 23 H45 MOL A 1 15.384 13.051 -0.972 1.00 0.00
ATOM 24 H47 MOL A 1 16.617 15.225 -1.336 1.00 0.00
ATOM 25 H49 MOL A 1 14.963 12.826 1.877 1.00 0.00
ATOM 26 H51 MOL A 1 14.416 14.107 1.024 1.00 0.00
ATOM 27 H53 MOL A 1 17.283 11.478 -0.533 1.00 0.00
ATOM 28 H55 MOL A 1 16.787 11.402 1.021 1.00 0.00
ATOM 29 H57 MOL A 1 15.644 16.308 1.135 1.00 0.00
ATOM 30 H59 MOL A 1 18.580 15.502 0.699 1.00 0.00
ATOM 31 H61 MOL A 1 18.779 15.702 -0.909 1.00 0.00
ATOM 32 H63 MOL A 1 12.639 12.559 1.402 1.00 0.00
ATOM 33 H65 MOL A 1 13.489 11.383 0.654 1.00 0.00
ATOM 34 H67 MOL A 1 12.942 12.664 -0.198 1.00 0.00
ATOM 35 H69 MOL A 1 16.147 9.425 -0.137 1.00 0.00
ATOM 36 H71 MOL A 1 15.308 10.315 -1.218 1.00 0.00
ATOM 37 H73 MOL A 1 14.813 10.240 0.336 1.00 0.00
ATOM 38 H75 MOL A 1 14.416 15.778 -1.350 1.00 0.00
ATOM 39 H77 MOL A 1 15.970 17.511 -1.469 1.00 0.00
ATOM 40 H79 MOL A 1 18.127 16.329 -0.220 1.00 0.00
ATOM 41 H81 MOL A 1 13.670 16.937 -0.477 1.00 0.00
ATOM 42 H83 MOL A 1 15.111 19.493 -0.597 1.00 0.00
ATOM 43 H85 MOL A 1 14.822 18.738 0.821 1.00 0.00
ATOM 44 H87 MOL A 1 17.464 19.025 -0.372 1.00 0.00
ATOM 45 H89 MOL A 1 17.046 18.414 1.084 1.00 0.00
ATOM 46 H91 MOL A 1 19.790 17.111 0.901 1.00 0.00
ATOM 47 H93 MOL A 1 11.061 16.245 -0.181 1.00 0.00
ATOM 48 H95 MOL A 1 11.755 14.775 -0.330 1.00 0.00
ATOM 49 H97 MOL A 1 11.863 15.855 -1.549 1.00 0.00
ATOM 50 H99 MOL A 1 12.104 17.461 1.010 1.00 0.00
ATOM 51 1H10 MOL A 1 20.753 19.303 0.523 1.00 0.00
ATOM 52 3H10 MOL A 1 21.921 18.690 -0.408 1.00 0.00
ATOM 53 5H10 MOL A 1 21.980 18.327 1.183 1.00 0.00
ATOM 54 7H10 MOL A 1 24.064 17.776 0.141 1.00 0.00
ATOM 55 9H10 MOL A 1 23.285 16.783 -0.895 1.00 0.00
ATOM 56 1H11 MOL A 1 23.345 16.420 0.696 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>

'''Synthesis route of Oseltamivir'''

[[Image:Tamiflu Synthesis1.JPG]]

As shown above, the synthesis of Oseltamivir require shikimic acid as a starting materials, and due to the shortage of this important substance, the production of tamiflu was reduced in 2005. However, in early 2006, a new synthetic route has been invented which does not involve the use of shikimic acid and it is called Corey synthesis.

[[image:Corey Synthesis of tamiflu1.JPG]]

References

1. http://en.wikipedia.org/wiki/Oseltamivir
2. http://www.rxlist.com/drugs/mono-5294-OSELTAMIVIR+-+ORAL.aspx? drugid=17765&drugname=Tamiflu+Oral
3. http://www.netdoctor.co.uk/medicines/100004852.html
4. http://www.webmd.com/drugs/mono-5294-OSELTAMIVIR+-+ORAL.aspx?drugid=17765&drugname=Tamiflu

It:Oseltamivir

2006-12-06T18:52:13Z

Hcy05:

It:Oseltamivir

2006-12-06T18:51:46Z

Hcy05:

It:Oseltamivir

2006-12-06T18:51:15Z

Hcy05:

It:Oseltamivir

2006-12-06T18:46:51Z

Hcy05:

Oseltamivir is specially invented for treatment of influenzavirus A and B. It is neuraminidase inhibitors which stop the virus emerge from the infected cell. It is the first neuraminidase inhibitor which is orally active. It was first developed by Gilead sciences and is now available on the market with the trade name – tamiflu. However, in order to get this drug, prescription is needed.

Usage

When Tamiflu was first invented, it was used in treatment or prevention of influenza. Flu virus cause several symptoms to human body.
- Stuff nose
- Cough
- Sore throat
- Fever or chills
- Aches
- Tiredness
The use of tamiflu can reduce the recovery times and help the body to relief the symptoms. If the person is not infected by flu virus, he can still take tamiflu to prevent or minimise the chances of infection of influenza.

Dosage

The normal dosage of tamiflu if a person is infected by influenza is to take 2 tablets for in 5 days. For the prevention of flu (especially for those who is going to expose to the flu) is to take one tablet for at least a week.

How does it works

As mentioned above, Oseltamivir is a neuraminidase inhibitor. It binds to the surface of neuraminidase and stops its normal function. Neuraminidase is an enzyme which controls the release of the newly formed virus from the cell. So Oseltamivir does not actually kills the virus or stop its activity, it only stops the virus getting out from the cell. Therefore, when a patient is infected by flu virus, the virus can still replicate even a patient take tamiflu. However, the number of virus will not be huge enough to cause any flu symptoms to the patient if tamiflu is taken at the early stage. This has a very important consequence to the human body. With the help of tamiflu, the flu virus will be acuminated in a small area so the human immune systems can deal with the virus more efficiently.

Avian influenza

In 2005, tamiflu was first used in H5N1 influenza. However, normal dosage results in viral resistance. Therefore, patients required a higher doses and longer period of the drugs and it works quite well.

'''Structure of Oseltamivir'''

[[Image:Oseltamivir.bmp]]

==3D Structure==
<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 O1 MOL A 1 16.915 13.894 0.164 1.00 0.00
ATOM 2 C2 MOL A 1 15.808 12.929 -0.075 1.00 0.00
ATOM 3 C3 MOL A 1 16.850 15.311 -0.367 1.00 0.00
ATOM 4 C4 MOL A 1 14.629 13.131 0.985 1.00 0.00
ATOM 5 C5 MOL A 1 16.487 11.497 0.072 1.00 0.00
ATOM 6 C6 MOL A 1 15.676 16.256 0.137 1.00 0.00
ATOM 7 C7 MOL A 1 18.214 15.943 -0.120 1.00 0.00
ATOM 8 C8 MOL A 1 13.307 12.366 0.684 1.00 0.00
ATOM 9 C9 MOL A 1 15.611 10.259 -0.267 1.00 0.00
ATOM 10 N10 MOL A 1 14.381 15.721 -0.352 1.00 0.00
ATOM 11 C11 MOL A 1 15.933 17.639 -0.478 1.00 0.00
ATOM 12 C12 MOL A 1 18.374 17.256 0.063 1.00 0.00
ATOM 13 C13 MOL A 1 13.112 16.285 0.036 1.00 0.00
ATOM 14 N14 MOL A 1 14.886 18.618 -0.170 1.00 0.00
ATOM 15 C15 MOL A 1 17.219 18.192 0.124 1.00 0.00
ATOM 16 C16 MOL A 1 19.696 17.841 0.224 1.00 0.00
ATOM 17 C17 MOL A 1 11.842 15.745 -0.555 1.00 0.00
ATOM 18 O18 MOL A 1 13.058 17.198 0.865 1.00 0.00
ATOM 19 O19 MOL A 1 20.846 17.077 0.102 1.00 0.00
ATOM 20 O20 MOL A 1 19.789 19.052 0.436 1.00 0.00
ATOM 21 C21 MOL A 1 21.980 17.947 0.258 1.00 0.00
ATOM 22 C22 MOL A 1 23.282 17.163 0.030 1.00 0.00
ATOM 23 H45 MOL A 1 15.384 13.051 -0.972 1.00 0.00
ATOM 24 H47 MOL A 1 16.617 15.225 -1.336 1.00 0.00
ATOM 25 H49 MOL A 1 14.963 12.826 1.877 1.00 0.00
ATOM 26 H51 MOL A 1 14.416 14.107 1.024 1.00 0.00
ATOM 27 H53 MOL A 1 17.283 11.478 -0.533 1.00 0.00
ATOM 28 H55 MOL A 1 16.787 11.402 1.021 1.00 0.00
ATOM 29 H57 MOL A 1 15.644 16.308 1.135 1.00 0.00
ATOM 30 H59 MOL A 1 18.580 15.502 0.699 1.00 0.00
ATOM 31 H61 MOL A 1 18.779 15.702 -0.909 1.00 0.00
ATOM 32 H63 MOL A 1 12.639 12.559 1.402 1.00 0.00
ATOM 33 H65 MOL A 1 13.489 11.383 0.654 1.00 0.00
ATOM 34 H67 MOL A 1 12.942 12.664 -0.198 1.00 0.00
ATOM 35 H69 MOL A 1 16.147 9.425 -0.137 1.00 0.00
ATOM 36 H71 MOL A 1 15.308 10.315 -1.218 1.00 0.00
ATOM 37 H73 MOL A 1 14.813 10.240 0.336 1.00 0.00
ATOM 38 H75 MOL A 1 14.416 15.778 -1.350 1.00 0.00
ATOM 39 H77 MOL A 1 15.970 17.511 -1.469 1.00 0.00
ATOM 40 H79 MOL A 1 18.127 16.329 -0.220 1.00 0.00
ATOM 41 H81 MOL A 1 13.670 16.937 -0.477 1.00 0.00
ATOM 42 H83 MOL A 1 15.111 19.493 -0.597 1.00 0.00
ATOM 43 H85 MOL A 1 14.822 18.738 0.821 1.00 0.00
ATOM 44 H87 MOL A 1 17.464 19.025 -0.372 1.00 0.00
ATOM 45 H89 MOL A 1 17.046 18.414 1.084 1.00 0.00
ATOM 46 H91 MOL A 1 19.790 17.111 0.901 1.00 0.00
ATOM 47 H93 MOL A 1 11.061 16.245 -0.181 1.00 0.00
ATOM 48 H95 MOL A 1 11.755 14.775 -0.330 1.00 0.00
ATOM 49 H97 MOL A 1 11.863 15.855 -1.549 1.00 0.00
ATOM 50 H99 MOL A 1 12.104 17.461 1.010 1.00 0.00
ATOM 51 1H10 MOL A 1 20.753 19.303 0.523 1.00 0.00
ATOM 52 3H10 MOL A 1 21.921 18.690 -0.408 1.00 0.00
ATOM 53 5H10 MOL A 1 21.980 18.327 1.183 1.00 0.00
ATOM 54 7H10 MOL A 1 24.064 17.776 0.141 1.00 0.00
ATOM 55 9H10 MOL A 1 23.285 16.783 -0.895 1.00 0.00
ATOM 56 1H11 MOL A 1 23.345 16.420 0.696 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>

Synthesis route of Oseltamivir

[[Image:Tamiflu Synthesis1.JPG]]

It:Oseltamivir

2006-12-06T18:46:09Z

Hcy05:

It:Oseltamivir

2006-12-06T18:38:17Z

Hcy05:

Oseltamivir is specially invented for treatment of influenzavirus A and B. It is neuraminidase inhibitors which stop the virus emerge from the infected cell. It is the first neuraminidase inhibitor which is orally active. It was first developed by Gilead sciences and is now available on the market with the trade name – tamiflu. However, in order to get this drug, prescription is needed.

Usage
When Tamiflu was first invented, it was used in treatment or prevention of influenza. Flu virus cause several symptoms to human body.
- Stuff nose
- Cough
- Sore throat
- Fever or chills
- Aches
- Tiredness
The use of tamiflu can reduce the recovery times and help the body to relief the symptoms. If the person is not infected by flu virus, he can still take tamiflu to prevent or minimise the chances of infection of influenza.

Dosage
The normal dosage of tamiflu if a person is infected by influenza is to take 2 tablets for in 5 days. For the prevention of flu (especially for those who is going to expose to the flu) is to take one tablet for at least a week.

How does it works
As mentioned above, Oseltamivir is a neuraminidase inhibitor. It binds to the surface of neuraminidase and stops its normal function. Neuraminidase is an enzyme which controls the release of the newly formed virus from the cell. So Oseltamivir does not actually kills the virus or stop its activity, it only stops the virus getting out from the cell. Therefore, when a patient is infected by flu virus, the virus can still replicate even a patient take tamiflu. However, the number of virus will not be huge enough to cause any flu symptoms to the patient if tamiflu is taken at the early stage. This has a very important consequence to the human body. With the help of tamiflu, the flu virus will be acuminated in a small area so the human immune systems can deal with the virus more efficiently.

Avian influenza
In 2005, tamiflu was first used in H5N1 influenza. However, normal dosage results in viral resistance. Therefore, patients required a higher doses and longer period of the drugs and it works quite well.

'''Structure of Oseltamivir'''

[[Image:Oseltamivir.bmp]]

==3D Structure==
<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 O1 MOL A 1 16.915 13.894 0.164 1.00 0.00
ATOM 2 C2 MOL A 1 15.808 12.929 -0.075 1.00 0.00
ATOM 3 C3 MOL A 1 16.850 15.311 -0.367 1.00 0.00
ATOM 4 C4 MOL A 1 14.629 13.131 0.985 1.00 0.00
ATOM 5 C5 MOL A 1 16.487 11.497 0.072 1.00 0.00
ATOM 6 C6 MOL A 1 15.676 16.256 0.137 1.00 0.00
ATOM 7 C7 MOL A 1 18.214 15.943 -0.120 1.00 0.00
ATOM 8 C8 MOL A 1 13.307 12.366 0.684 1.00 0.00
ATOM 9 C9 MOL A 1 15.611 10.259 -0.267 1.00 0.00
ATOM 10 N10 MOL A 1 14.381 15.721 -0.352 1.00 0.00
ATOM 11 C11 MOL A 1 15.933 17.639 -0.478 1.00 0.00
ATOM 12 C12 MOL A 1 18.374 17.256 0.063 1.00 0.00
ATOM 13 C13 MOL A 1 13.112 16.285 0.036 1.00 0.00
ATOM 14 N14 MOL A 1 14.886 18.618 -0.170 1.00 0.00
ATOM 15 C15 MOL A 1 17.219 18.192 0.124 1.00 0.00
ATOM 16 C16 MOL A 1 19.696 17.841 0.224 1.00 0.00
ATOM 17 C17 MOL A 1 11.842 15.745 -0.555 1.00 0.00
ATOM 18 O18 MOL A 1 13.058 17.198 0.865 1.00 0.00
ATOM 19 O19 MOL A 1 20.846 17.077 0.102 1.00 0.00
ATOM 20 O20 MOL A 1 19.789 19.052 0.436 1.00 0.00
ATOM 21 C21 MOL A 1 21.980 17.947 0.258 1.00 0.00
ATOM 22 C22 MOL A 1 23.282 17.163 0.030 1.00 0.00
ATOM 23 H45 MOL A 1 15.384 13.051 -0.972 1.00 0.00
ATOM 24 H47 MOL A 1 16.617 15.225 -1.336 1.00 0.00
ATOM 25 H49 MOL A 1 14.963 12.826 1.877 1.00 0.00
ATOM 26 H51 MOL A 1 14.416 14.107 1.024 1.00 0.00
ATOM 27 H53 MOL A 1 17.283 11.478 -0.533 1.00 0.00
ATOM 28 H55 MOL A 1 16.787 11.402 1.021 1.00 0.00
ATOM 29 H57 MOL A 1 15.644 16.308 1.135 1.00 0.00
ATOM 30 H59 MOL A 1 18.580 15.502 0.699 1.00 0.00
ATOM 31 H61 MOL A 1 18.779 15.702 -0.909 1.00 0.00
ATOM 32 H63 MOL A 1 12.639 12.559 1.402 1.00 0.00
ATOM 33 H65 MOL A 1 13.489 11.383 0.654 1.00 0.00
ATOM 34 H67 MOL A 1 12.942 12.664 -0.198 1.00 0.00
ATOM 35 H69 MOL A 1 16.147 9.425 -0.137 1.00 0.00
ATOM 36 H71 MOL A 1 15.308 10.315 -1.218 1.00 0.00
ATOM 37 H73 MOL A 1 14.813 10.240 0.336 1.00 0.00
ATOM 38 H75 MOL A 1 14.416 15.778 -1.350 1.00 0.00
ATOM 39 H77 MOL A 1 15.970 17.511 -1.469 1.00 0.00
ATOM 40 H79 MOL A 1 18.127 16.329 -0.220 1.00 0.00
ATOM 41 H81 MOL A 1 13.670 16.937 -0.477 1.00 0.00
ATOM 42 H83 MOL A 1 15.111 19.493 -0.597 1.00 0.00
ATOM 43 H85 MOL A 1 14.822 18.738 0.821 1.00 0.00
ATOM 44 H87 MOL A 1 17.464 19.025 -0.372 1.00 0.00
ATOM 45 H89 MOL A 1 17.046 18.414 1.084 1.00 0.00
ATOM 46 H91 MOL A 1 19.790 17.111 0.901 1.00 0.00
ATOM 47 H93 MOL A 1 11.061 16.245 -0.181 1.00 0.00
ATOM 48 H95 MOL A 1 11.755 14.775 -0.330 1.00 0.00
ATOM 49 H97 MOL A 1 11.863 15.855 -1.549 1.00 0.00
ATOM 50 H99 MOL A 1 12.104 17.461 1.010 1.00 0.00
ATOM 51 1H10 MOL A 1 20.753 19.303 0.523 1.00 0.00
ATOM 52 3H10 MOL A 1 21.921 18.690 -0.408 1.00 0.00
ATOM 53 5H10 MOL A 1 21.980 18.327 1.183 1.00 0.00
ATOM 54 7H10 MOL A 1 24.064 17.776 0.141 1.00 0.00
ATOM 55 9H10 MOL A 1 23.285 16.783 -0.895 1.00 0.00
ATOM 56 1H11 MOL A 1 23.345 16.420 0.696 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>

File:Corey Synthesis of tamiflu1.JPG

2006-12-06T18:34:47Z

Hcy05:

File:Tamiflu Synthesis1.JPG

2006-12-06T18:34:26Z

Hcy05:

It:Oseltamivir

2006-11-17T14:06:10Z

Hcy05:

Oseltamivir (INN) (IPA: [ɒsɛlˈtæmɪvir]) is an antiviral drug that is used in the treatment and prophylaxis of both Influenzavirus A and Influenzavirus B. Like zanamivir, oseltamivir is a neuraminidase inhibitor. It acts as a transition-state analogue inhibitor of influenza neuraminidase, preventing new viruses from emerging from infected cells.

Oseltamivir was the first orally active neuraminidase inhibitor commercially developed. It is a prodrug, which is hydrolysed hepatically to the active metabolite, the free carboxylate of oseltamivir (GS4071). It was developed by Gilead Sciences and is currently marketed by Hoffmann-La Roche (Roche) under the trade name Tamiflu. It is generally available by prescription only.

With increasing fears about the potential for a new influenza pandemic, oseltamivir has received substantial media attention. Production capacity is limited, and governments (and even some private individuals) are stockpiling the drug.

'''Structure of Oseltamivir'''
[[Image:Oseltamivir.bmp]]

'''How does it works'''

Oseltamivir is a neuraminidase inhibitor. By blocking the activity of the neuraminidase, Oseltamivir prevents new viral particles from being released by infected cells.

'''Use in avian influenza'''

It has been found that the standard recommended dose incompletely suppresses viral replication in at least some patients with H5N1 influenza, rendering therapy ineffective and increasing the risk of viral resistance. Accordingly, it has been suggested that higher doses and longer durations of therapy should be used for treatment of patients with the H5N1 virus.

'''Veterinary use'''

Oseltamivir appears to be active against canine parvovirus, feline panleukopenia, the canine respiratory complex known as "kennel cough," and the emerging disease dubbed "canine flu", an equine virus that began affecting dogs in 2005. Veterinary investigation of its use for canine parvo and canine flu is ongoing, but many shelters and rescue groups have reported great success employing oseltamivir in the early stages of these illnesses.

'''Chemical synthesis'''

The current production method includes two reaction steps with potentially hazardous azides. A reported azide-free Roche synthesis of tamiflu is summarised graphically below:

[[Image:410px-Tamiflu2.gif]]

'''Corey synthesis'''

[[Image:Corey_oseltamivir_synthesis.PNG]]

'''References'''

1.http://en.wikipedia.org/wiki/Oseltamivir

It:Oseltamivir

2006-11-17T14:03:27Z

Hcy05:

File:Corey oseltamivir synthesis.PNG

2006-11-17T14:02:58Z

Hcy05:

It:Oseltamivir

2006-11-17T13:59:39Z

Hcy05:

It:Oseltamivir

2006-11-17T13:59:15Z

Hcy05:

File:Corey oseltamivir synthesis.png

2006-11-17T13:58:01Z

Hcy05:

It:Oseltamivir

2006-11-17T13:50:01Z

Hcy05:

File:410px-Tamiflu2.gif

2006-11-17T13:48:37Z

Hcy05:

It:Oseltamivir

2006-11-17T13:47:48Z

Hcy05:

Oseltamivir (INN) (IPA: [ɒsɛlˈtæmɪvir]) is an antiviral drug that is used in the treatment and prophylaxis of both Influenzavirus A and Influenzavirus B. Like zanamivir, oseltamivir is a neuraminidase inhibitor. It acts as a transition-state analogue inhibitor of influenza neuraminidase, preventing new viruses from emerging from infected cells.

Oseltamivir was the first orally active neuraminidase inhibitor commercially developed. It is a prodrug, which is hydrolysed hepatically to the active metabolite, the free carboxylate of oseltamivir (GS4071). It was developed by Gilead Sciences and is currently marketed by Hoffmann-La Roche (Roche) under the trade name Tamiflu. It is generally available by prescription only.

With increasing fears about the potential for a new influenza pandemic, oseltamivir has received substantial media attention. Production capacity is limited, and governments (and even some private individuals) are stockpiling the drug.

'''Structure of Oseltamivir'''
[[Image:Oseltamivir.bmp]]

'''How does it works'''
Oseltamivir is a neuraminidase inhibitor. By blocking the activity of the neuraminidase, Oseltamivir prevents new viral particles from being released by infected cells.

'''Use in avian influenza'''

It has been found that the standard recommended dose incompletely suppresses viral replication in at least some patients with H5N1 influenza, rendering therapy ineffective and increasing the risk of viral resistance. Accordingly, it has been suggested that higher doses and longer durations of therapy should be used for treatment of patients with the H5N1 virus.

'''Veterinary use'''
Oseltamivir appears to be active against canine parvovirus, feline panleukopenia, the canine respiratory complex known as "kennel cough," and the emerging disease dubbed "canine flu", an equine virus that began affecting dogs in 2005. Veterinary investigation of its use for canine parvo and canine flu is ongoing, but many shelters and rescue groups have reported great success employing oseltamivir in the early stages of these illnesses.

'''Chemical synthesis'''
The current production method includes two reaction steps with potentially hazardous azides. A reported azide-free Roche synthesis of tamiflu is summarised graphically below:

It:Oseltamivir

2006-11-17T11:53:01Z

Hcy05:

It:Oseltamivir

2006-11-17T11:52:10Z

Hcy05:

File:Oseltamivir.bmp

2006-11-17T11:49:46Z

Hcy05:

It:Oseltamivir

2006-11-17T11:48:55Z

Hcy05:

It:projects

2006-11-17T11:37:53Z

Hcy05: /* Supplemental Project Page */

__FORCETOC__

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! bgcolor="cyan" |Project Number
! bgcolor="cyan" |General Keywords
|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
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|-
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|-
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|-
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|-
| bgcolor="#CCFF00" |11
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|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H3N-BH3 (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
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|-
| bgcolor="#CCFF00" |18
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|-
| bgcolor="#CCFF00" |19
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[[R & S Phrases]]

It:wilkinson

2006-10-23T15:12:42Z

Hcy05: /* Structure and Synthesis */

It:wilkinson

2006-10-23T14:35:42Z

Hcy05: /* Structure and Synthesis */

It:wilkinson

2006-10-23T14:32:45Z

Hcy05:

It:wilkinson

2006-10-23T14:31:04Z

Hcy05: /* Structure and Synthesis */

It:wilkinson

2006-10-23T14:16:26Z

Hcy05: /* Wilkinson's Catalyst */

=====Wilkinson's Catalyst=====

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

<jmol>
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<size>400</size>
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<script>zoom 100; ball and Stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>wilkinsoncat.mol

104112 0 0 0 1 V2000
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0
1.1431 1.9689 -3.0329 C 0 0 0 0 0
0.5202 1.6759 -4.2514 C 0 0 0 0 0
0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
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3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
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55 56 1 1 0 0
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56101 1 0 0 0
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58 59 2 0 0 0
58103 1 1 0 0
59104 1 0 0 0
M END</inlineContents>
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</jmol>

The formula for Wilkinsons Catalyst is C54H45ClP3Rh

'''An example of the Wilkinson Catalyst reaction:'''
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2].

'''Structure and Synthesis'''

This compound RhCl(PPh3) is a ''square planar'', 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of ''rhodium trichloride'' with ''triphenylphosphine''. The synthesis is conducted in refluxing ethanol.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

'''Chart of Catalystic Properties'''
[[Image:Wilkinson_Catalyst.GIF|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

Initial search result citation1

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

--[[User:Mjl105|Mjl105]] 15:36, 20 October 2006 (BST)

It:wilkinson

2006-10-23T14:13:30Z

Hcy05: /* Wilkinson's Catalyst */

=====Wilkinson's Catalyst=====

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and Stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>wilkinsoncat.mol

104112 0 0 0 1 V2000
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0
1.1431 1.9689 -3.0329 C 0 0 0 0 0
0.5202 1.6759 -4.2514 C 0 0 0 0 0
0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
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1.6930 -2.8219 1.9100 C 0 0 0 0 0
2.4316 -2.9296 3.0942 C 0 0 0 0 0
2.0614 -3.8291 4.0967 C 0 0 0 0 0
0.9548 -4.6600 3.9209 C 0 0 0 0 0
0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
5.9780 0.5179 2.1402 C 0 0 0 0 0
4.7485 0.6342 2.7897 C 0 0 0 0 0
3.6218 -0.0078 2.2721 C 0 0 0 0 0
2.1677 -1.6384 0.5153 P 0 3 0 0 0
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0
-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
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-0.1187 3.2408 0.9128 C 0 0 0 0 0
0.2956 4.5106 1.3177 C 0 0 0 0 0
0.0355 5.6176 0.5096 C 0 0 0 0 0
-0.6485 5.4438 -0.6940 C 0 0 0 0 0
-1.0576 4.1696 -1.0938 C 0 0 0 0 0
-2.8463 1.0234 0.2603 C 0 0 0 0 0
-3.5530 -0.1726 0.0865 C 0 0 0 0 0
-4.7370 -0.4120 0.7866 C 0 0 0 0 0
-5.2370 0.5519 1.6631 C 0 0 0 0 0
-4.5463 1.7523 1.8348 C 0 0 0 0 0
-3.3593 1.9856 1.1369 C 0 0 0 0 0
0.3800 0.6415 -4.5854 H 0 0 0 0 0
-0.4429 2.4148 -6.0491 H 0 0 0 0 0
-0.1140 4.8185 -5.4421 H 0 0 0 0 0
1.0451 5.3954 -3.3036 H 0 0 0 0 0
1.8069 3.6360 -1.7841 H 0 0 0 0 0
4.3314 1.8231 -3.0516 H 0 0 0 0 0
6.1490 3.2015 -2.0911 H 0 0 0 0 0
6.0335 3.9578 0.2887 H 0 0 0 0 0
4.0574 3.3374 1.6885 H 0 0 0 0 0
2.2746 1.8922 0.7534 H 0 0 0 0 0
0.6584 -1.3179 -3.8324 H 0 0 0 0 0
1.6220 -2.9883 -5.3441 H 0 0 0 0 0
4.0844 -3.4247 -5.3442 H 0 0 0 0 0
5.5606 -2.1234 -3.7998 H 0 0 0 0 0
4.6167 -0.4073 -2.3293 H 0 0 0 0 0
0.5148 -2.8211 -1.5913 H 0 0 0 0 0
0.8200 -4.7186 -3.1578 H 0 0 0 0 0
2.9459 -6.0336 -3.1421 H 0 0 0 0 0
4.7305 -5.4811 -1.4819 H 0 0 0 0 0
4.4065 -3.6300 0.1274 H 0 0 0 0 0
3.3326 -2.3235 3.2645 H 0 0 0 0 0
2.6540 -3.8952 5.0239 H 0 0 0 0 0
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0.0300 -3.6842 0.7953 H 0 0 0 0 0
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7.0365 -0.3324 0.4516 H 0 0 0 0 0
6.8657 1.0364 2.5360 H 0 0 0 0 0
4.6632 1.2478 3.7011 H 0 0 0 0 0
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59104 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

The formula for Wilkinsons Catalyst is C54H45ClP3Rh

'''An example of the Wilkinson Catalyst reaction:'''
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2].

Structure and Synthesis

This compound RhCl(PPh3) is a square planar, 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of rhodium trichloride with triphenylphosphine. The synthesis is conducted in refluxing ethanol.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

Initial search result citation1

[[Image:Wilkinson_Catalyst.GIF|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]
1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

--[[User:Mjl105|Mjl105]] 15:36, 20 October 2006 (BST)

It:wilkinson

2006-10-23T14:12:01Z

Hcy05: /* Wilkinson's Catalyst */

=====Wilkinson's Catalyst=====

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and Stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>wilkinsoncat.mol

104112 0 0 0 1 V2000
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0
1.1431 1.9689 -3.0329 C 0 0 0 0 0
0.5202 1.6759 -4.2514 C 0 0 0 0 0
0.0553 2.6804 -5.1025 C 0 0 0 0 0
0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
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M END</inlineContents>
</jmolApplet>
</jmol>

The formula for Wilkinsons Catalyst is C54H45ClP3Rh

'''An example of the Wilkinson Catalyst reaction:'''
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'2. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2].

Structure and Synthesis

This compound RhCl(PPh3) is a square planar, 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of rhodium trichloride with triphenylphosphine. The synthesis is conducted in refluxing ethanol.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

Initial search result citation1

[[Image:Wilkinson Catalyst.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]
1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

--[[User:Mjl105|Mjl105]] 15:36, 20 October 2006 (BST)

File:Wilkinson Catalyst.GIF

2006-10-23T14:00:12Z

Hcy05:

It:wilkinson

2006-10-23T13:55:20Z

Hcy05: Addition of synthesis route and equation

=====Wilkinson's Catalyst=====

Wilkinson's catalyst is ''Tris(triphenylphosphine) rhodium(I) chloride'' or ''chloro-tris(triphenylphosphine) rhodium(i)'' the structure of which is shown in the picture below:

[[Image:WCat.gif|thumb|A gif picture of Tris(triphenylphosphine) rhodium(I) chloride (Wilkinson's catalyst) from eMolecules.com]]

And here is a 3D picture:

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; ball and Stick on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>wilkinsoncat.mol

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1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
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5.3078 2.8854 -1.4532 C 0 0 0 0 0
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M END</inlineContents>
</jmolApplet>
</jmol>

The formula for Wilkinsons Catalyst is C54H45ClP3Rh

'''An example of the Wilkinson Catalyst reaction:'''
The Wilkinson catalyst RhCl(PPh3)3 is known to react with pyridine to lead to the 'reductive coupling of aldehydes'. The pyridine molecule is able to react well with the catalyst since it is able to exchange its ligands with the catalyst, for example [RhCl(py)(PPh3)2].

Structure and Synthesis

This compound RhCl(PPh3) is a square planar, 16-electron complex, and is usually isolated in the form of a red-violet crystalline solid from the reaction of rhodium trichloride with triphenylphosphine. The synthesis is conducted in refluxing ethanol.

RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 -> RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

Initial search result citation1

1. [http://www.sciencedirect.com/science/article/B6THD-4KWK10C-1/2/23598dfb1e674011a2e6aaef2ff7a4fe R. Acosta Ortiz, M. Sangermano, R. Bongiovanni, A. E. Garcia Valdez, L. B. Duarte, I. P. Saucedo and A. Priola, ''Progress in Organic Coatings'', 2006, '''57''', 159-164.]

----

--[[User:Mjl105|Mjl105]] 15:36, 20 October 2006 (BST)

File:RevisedCatCycle.png

2006-10-23T13:52:03Z

Hcy05: